Shark Tank: Copa Di Vino's Second Appearance Failed Due To The Owner's Behavior

James Martin made "Shark Tank" history by being the first to appear twice on the show, both times pitching his wine brand, Copa di Vino. His first presentation was on Season 2, where he seeks $600,000 for a 20% equity stake. While Martin sees value in the product itself, Kevin O'Leary believes it'd be more worthwhile to license the patented wine-by-the-glass design to other companies. The longtime shark slashes Martin's valuation, wanting 51% of the business for the $600,000. Martin refuses and walks out to the tune of O'Leary saying, "I am going to buy a $1,000 bottle of wine tonight, and I'm going to drink it because I am weeping for the opportunity lost."

Season 3 saw Martin's return, this time with an offer of $300,000 for 5%. With his company on track to surpass $5 million in sales, he needs the sharks' help to build another bottling line to account for the increased demand. O'Leary, Robert Herjavec, and Mark Cuban offer to come in together for $600,000 at 30%. Martin's ego ultimately gets in the way, giving the sharks the runaround instead of doing business.

Frustrated by the unnecessary drama, Cuban and Herjavec back out, with the latter even walking off-set. Barbara Corcoran perhaps puts it best, stating, "I'm having the same visceral reaction. For some reason ... I didn't like you then, and I don't like you now." It's likely that the other sharks would agree with that sentiment, with Copa di Vino's continued success having done little to change their minds about Martin himself.

It's not uncommon for an entrepreneur to stand their ground on "Shark Tank," but James Martin took things to a ridiculous level. From his condescending sips of wine to his unveiling of the "Dead Man Walking" blend to spite Kevin O'Leary, the entrepreneur's vendetta took priority over getting a deal. But even with Copa di Vino reaching upwards of $70 million in sales, the sharks don't think that any price tag could make working with Martin any easier.

In a 2017 interview with ABC News, the sharks considered Copa di Vino one of the deals they don't regret missing out on. His second appearance especially left a bad taste in their mouths, with Mark Cuban saying, "He knew we all were interested, and he was trying to be too cool, too smart. He was up there thinking he's the man."

Cuban's sentiment isn't too far off from Martin's own mindset. The entrepreneur was also interviewed, and his egocentric personality was on full display. "I had a hate for Kevin O'Leary, a level that wasn't healthy at all," Martin admitted. "And my opportunity to come back was also my chance to get the last word in and say, 'Look, you blew it, but I'm also gracious enough to give you a second chance.'" When asked if there was any regret in not partnering, the sharks gave a resounding no, believing that dealing with Martin on a regular basis would be torturous. Their interactions may have not resulted in a deal, but at least "Shark Tank" fans were gifted with some of the most entertaining segments in the show's history.